Dean Winters is an American actor best known for his role in the series ‘Oz’ and ‘Brooklyn Nine-Nine.’ While he was growing up, Dean did not have any ambition or interest in becoming an actor. His younger brother, Scott, was training to become an actor and Dean followed his footsteps and enrolled into acting school. He made his debut in 1995, appearing in the television series ‘Homicide: Life on the Street.’ He received his acting breakthrough in 1997, when he began appearing in the series ‘Oz,’ in a recurring role, which later became a regular role. Since then, Dean has appeared in series’ such as ‘Divorce,’ ‘Battle Creek’ and ‘Brooklyn Nine-Nine.’ In addition, he has also played supporting roles in films, such as ‘John Wick’ and ‘Don Peyote.’
Childhood & Early Life
Dean Winters was born Dean Gerard Winters, on July 20, 1964, in New York City, to Patrick and Magna Winters. His father worked as an electrical engineer while his mother was a housewife. He was raised along with two brothers and a sister. Both his brothers went on to work in the entertainment industry.
His mother passed away when Dean was still too young. He spent most of his childhood in Long Island. He attended ‘Hommocks Middle School,’ where he was schoolmates with actors Kevin and Matt Dillon.
Later, Dean moved to Arizona to live with his grandparents and attended ‘Chaparral High School,’ in Scottsdale. By then, he had no interest in acting or any other aspect of the performance arts.
He completed his high school graduation from ‘Brophy College Preparatory,’ in Phoenix. Following his graduation, he enrolled at ‘Colorado College.’ He then further went to London to study art history. Whole studying in London, he did modelling to earn some pocket money.
His younger brother, Scott, had started trying his hand for opportunities in acting, but Dean was still clueless about what he wanted to do with his life. Following his graduation from college, he moved back to Manhattan and started bartending in pubs and bars.
His younger brother, Scott, convinced Dean to take acting training under William Esper. He also did a summer intensive at the ‘Royal Academy of Dramatic Art,’ in London.
In his late 20s, Dean got inclined towards a career in acting. He did some theatre and also began auditioning for roles in films and television.
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Dean made his acting debut in 1995, playing a recurring role as ‘Tom Marans’ in the police procedural drama series ‘Homicide: Life on the Street.’ He reprised his role in three episodes of the series.
In the next few years, Dean landed a few more small roles in series’ such as ‘NYPD Blue’ and ‘The Playroom.’
In 1997, Dean landed a huge opportunity when he was selected to appear in a supporting role in the political thriller ‘Conspiracy Theory,’ which starred Mel Gibson. He played the role of Cleet in the film, which was a commercial and critical success. In the same year, Dean appeared playing another supporting role in the film ‘Lifebreath.’
While he was bartending in NYC, Dean and his brother Scott met and befriended writer Tom Fontana. Tom had written Dean’s part in the series ‘Homicide: Life on the Street.’ Tom offered a recurring role to Dean in his television series ‘Oz.’
‘Oz’ premiered in 1997, and Dean appeared in a recurring role as Ryan O’Reily. The series became acritical and commercial hit. Dean’s role was widely appreciated and hence his character was turned into a regular one. ‘Oz’ ran for 6 seasons and 56 episodes.
In 1999, Dean bagged the first leading role of his career in the Canadian comedy film ‘Undercover Angel.’ The film received average ratings.
As for his television career, he kept appearing in guest roles in series such as ‘New York Undercover’ and ‘Sex and the City.’
He received yet another major breakthrough in 1999, when he appeared in a recurring role as ‘Brian Cassidy’ in the police procedural drama series ‘Law & Order: Special Victims Unit.’ He appeared in a recurring role in 19 episodes, and also played a main character for 13 episodes.
In the 2000s, he appeared mostly in supporting roles in films such as ‘Brooklyn Bound,’ ‘Love Rome’ and ‘Dead Calling.’ He also appeared in the hugely successful film ‘P.S. I Love You.’
After playing guest roles in series’ such as ‘The Twilight Zone’ and ‘Third Watch,’ he appeared playing a lead role as ‘Johnny Gavin’ in the series ‘Rescue Me.’ He followed it with yet another recurring role in the 2006 series‘30 Rock.’ He played ‘Dennis Duffy’ in the series, which became an extremely popular character. He received a ‘Gold Derby’ nomination for ‘Best Guest Actor’ for his role in the series.
In 2008, he appeared in yet another recurring role, as ‘Charley Dixon’ in the series ‘Terminator: The Sarah Connor Chronicles.’
He has also appeared in recurring role as ‘Detective Keith 'The Vulture' Pembroke’ in the comedy police procedural series ‘Brooklyn Nine-Nine.’ In addition, he also appeared playing key roles in ‘Battle Creek’ and ‘Divorce.’
Family & Personal Life
Dean Winters suffered from a bad bacterial infection in 2009, and he suffered a cardiac arrest while he was being taken to hospital. He remained in intensive care for three weeks. During the next year, he developed Gangrene, which led to amputation of two toes and half of one thumb.
Dean Winters is said to have been in relationships with actress Jennifer Esposito and Maggie Marzigiliano. He is not married.